This invention relates to an anti-cancer agent and process for preparing for same. More particularly, this invention relates to beta-glycosyl C-Nucleoside compounds which have been found to inhibit the growth of leukemic cells. The compounds have been demonstrated to have anti-tumor activity and appear to have some anti-viral activity.
Methods for making N-Nucleosides similar to the C-Nucleosides, which are the subject of this invention, are well known and well practiced. These techniques basically involve fusing an appropriate sugar to an appropriate base to form the required compound. These techniques cannot be applied to C-Nucleosides because of the low reactivity of the carbon site when compared with the nitrogen site.
To form C-Nucleosides, it has been found convenient to start with an appropriately substituted sugar moiety and "build" the desired base. However, known schemes for accomplishing this are difficult to follow and have only limited applicability because of the reagents used (see for example Gupta et al Abstract No. 40, 175 A.C.S. National Meeting, Anaheim, Calif., Mar. 13-17, 1978). Another procedure was also applied to the synthesis of a closely related compound to the inventive compounds. in Lim et al, Tetrahedron Letters, Volumn 21, pp 1013-1016 (1980). However, this compound has been found to have essentially no antitumor activity. For comparison, this compound is included in Table 1 showing relative inhibition activity for various inventive compounds (X--NH, R.sub.1 .dbd.OH).